Some of the best tenants I started on a month to month and then transitioned them to year leases. 

It has not been smooth at all as most tenants do not want to pay.

I'm trying to decide when or if I should transition from "building the portfolio" and acquiring properties and move to paying down the loans and building cash flow. 

Great to hear you are looking to transition out of your job to go into REI full-time.

Find yourself a great property manager and remote ownership works smoothly. 

The structure of the deal is a double close, and I intend on using transitional funding. 

Agreed @Nate Marshall - I chose the "guru" route to level-up my portfolio, brrrrr stopped working for me as frequently and since becoming a mom, I didn't feel as comfortable flying to locations where I could get the 1% rule so I've transitioned to flipping and enrolled in a course so I can be competitive in a HCOL cityLastly, though I'm not an influencer, I do enjoy sharing my projects on social media (like most people who take pride in their work).

After over 30 years here, I've seen it transition from cash flow to appreciation. 

I know know any path in this industry will be difficult but transitioning and applying the same amount of hours I work now, I'm sure it will lead to success eventually.

I am moving out of my primary residence of 5 years, and transitioning it to a rental property.